5-allyl-5,11-dihydro-10H-dibenzo[b,f]azepin-10-one -Drug Synthesis Database

【结构式】

【分子编号】48672

【品名】5-allyl-5,11-dihydro-10H-dibenzo[b,f]azepin-10-one

【CA登记号】

【分子式】C₁₇H₁₅NO

【分子量】249.31224

【元素组成】C 81.9% H 6.06% N 5.62% O 6.42%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(XI)

Syntheses of intermediate (XI), 5-allyl-10,11-dihydro-5H-dibenz[b,f]azepin-10-one: Cyclization of 2-[N-allyl-N-(2-methylphenyl)amino]-N,N-dimethylbenzamide (IX) or 2-[N-allyl-N-(2-methylphenyl)amino]-N,N-diethylbenzamide (X) by means of LDA and TMEDA in THF.

参考文献中间体

合成目标

【1】 Lohse, O.; Kaufmann, D.; France, J.; Beutler, U.; Funfschilling, P.; Zaugg, W.; Furet, P.; New synthesis of oxcarbazepine via remote metalation of protected N-o-tolyl-anthranilamide derivatives. Tetrahedron Lett 2001, 42, 3, 385.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(IX)	48670	2-(allyl-2-methylanilino)-N,N-dimethylbenzamide	C₁₉H₂₂N₂O	详情	详情
(X)	48671	2-(allyl-2-methylanilino)-N,N-diethylbenzamide	C₂₁H₂₆N₂O	详情	详情
(XI)	48672	5-allyl-5,11-dihydro-10H-dibenzo[b,f]azepin-10-one	C₁₇H₁₅NO	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XI)

Finally, deprotection of either intermediate (V) with TMS-Cl and NaI, intermediate (VIII) with TiCl4 or intermediate (XI) with Rh(PPh3)3Cl give, in all cases, 10,11-dihydro-5H-dibenz[b,f]azepin-10-one (XII), which is finally treated with chlorosulfonyl isocyanate to afford oxcarbazepine.

参考文献中间体

合成目标

【1】 Lohse, O.; Kaufmann, D.; France, J.; Beutler, U.; Funfschilling, P.; Zaugg, W.; Furet, P.; New synthesis of oxcarbazepine via remote metalation of protected N-o-tolyl-anthranilamide derivatives. Tetrahedron Lett 2001, 42, 3, 385.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(V)	48665	5-benzyl-5,11-dihydro-10H-dibenzo[b,f]azepin-10-one		C₂₁H₁₇NO	详情	详情
(VIII)	48669	5-(4-methoxybenzyl)-5,11-dihydro-10H-dibenzo[b,f]azepin-10-one		C₂₂H₁₉NO₂	详情	详情
(XI)	48672	5-allyl-5,11-dihydro-10H-dibenzo[b,f]azepin-10-one		C₁₇H₁₅NO	详情	详情
(XII)	48673	10H-Dibenz[b,f]azepin-10-one,5,11-dihydro-;10-Oxo-10,11-Dihydro-5H-dibenz[b,f]azepine;5,11-dihydro-10H-dibenzo[b,f]azepin-10-one	21737-58-6	C₁₄H₁₁NO	详情	详情

合成路线3

该中间体在本合成路线中的序号：(II)

参考文献中间体

合成目标

【1】 Lohse O, Beutler U, Fuenfschilling P, et al.2001. New syhthesis of oxcarbazepine via remote metalation of protected N-(ortho-tolyl) anthranilamide derivatives. Tetrahedron Lett,42:385-389.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	69534	2-(allyl(o-tolyl)amino)-N,N-dimethylbenzamide		C₁₉H₂₂N₂O	详情	详情
(II)	48672	5-allyl-5,11-dihydro-10H-dibenzo[b,f]azepin-10-one		C₁₇H₁₅NO	详情	详情

Extended Information